Ring-opening process for preparation of 2-chlorosulfinyl azetidi

Details Ring-opening process for preparation of 2-chlorosulfinyl azetidi Ring-opening process for preparation of 2-chlorosulfinyl azetidi

1990-03-07

1991-12-03

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540359, C07D20595, C07D50114, C07B 4504

Patent

active

050701959

ABSTRACT:
An improved method for preparing 2-chlorosulfinyl azetidine-4-one comprises heating a penicillin sulfoxide ester with an N-chlorohalogenating agent at a temperature of about 75.degree. C. to about 140.degree. in an inert organic solvent, and in the presence of an organic solvent insoluble, strongly basic ion exchange resin. Desirably, the ion exchange resin comprises a styrene-divinyl benzane copolymer which is about 2 to 16% cross-linked and incorporates a quaternary ammonium functionality. Such ion exchange resins are commercially available. The 2-chlorosulfinyl azetidine-4-one which is produced by this method can be cyclized in the presence of a Friedel-Crafts catalysts to afford the 3-exomethylene cepham sulfoxide ester in yields of 80-90%.

REFERENCES:
patent: 3993646 (1976-11-01), Kamiya et al.
patent: 4091210 (1978-05-01), Kamiya et al.
patent: 4289695 (1981-09-01), Chou

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